Educating Cassidy Ch. 01

"You really have this all planned out, don't you?"

"I've been thinking about it for a long time, I just didn't know who I was going to do it with. But then I saw you standing there in front of class and realized you would be perfect. You are in good shape, single, and mature enough to understand the situation without getting all possessive. You still good with this?"

"So far, you've been more than exciting and have a rational explanation for every step of the process you've worked out."

"Good, so let's move onto the next step."

With that she climbed onto the bed and put her knees on either side of me. She rubbed her slit up and down my shaft slowly, the latex muffling the sensations, a bit frustrating. After a couple of minutes of this teasing, she moved a bit further up. With her hand she repositioned my penis at the entrance of her tunnel and slowly slid back down. Considering that she had a couple of children, it was pretty tight and I moaned with lust as she sank down onto my shaft. Without moving her hips, I felt the muscles in her vagina start to massage my cock, bringing it to full hardness. Her hips began to rock forward and back. After another few minutes, she leaned back and leaned on her arms, I could see her breasts bouncing up and down as she started thrusting up and down several inches. Sweat was starting to bead up on her face, and her nipples were shrinking up into tight little beads. It was almost ten minutes before she locked up and screamed, a red flush racing across her face and chest as she reached orgasm. It set me over the edge as well, my whole body shuddering with ecstasy. To say I was totally spent would have been an understatement.

She slowly untangled herself, my limp penis plopping out of her as she moved. Gwen's color had returned to normal, but she was still breathing heavily. It took some effort, but she unfastened my legs, which was a relief. It took a few more minutes and she got the cuffs off my arms, I stretched my sore shoulders and hips as I stood up. It had been almost an hour and a half since she had arrived and in that time she had pulled three orgasms out of me, and had two good ones herself. I moved the bathroom and took care of the condom. I stuck my head into the room, "I'm going to shower, want to join me?"

She nodded and slid into the large space with me as the warm water cascaded over us. It was pretty low key, we did soap each other up, and it gave me a chance to really look her over. No doubt she was beautiful, her belly tighter than I would have expected. And her good looks didn't change close up. Gwen kept her hair dry, but we got clean and dried each other off. She retrieved her underwear and put it on, leaning on me for a moment as she lifted each leg. It was incredibly sexy, even though I was spent. I grabbed a pair of shorts and she stopped me.

"Not yet, Al, one more thing." Gwen went to her bag and returned with something. "I'm not going to demand to see the doctor's note that you are disease free, I'll trust you on that, but I'm also not going to take any risks. So for the next few weeks, you're going to wear this." With that she showed me a cock cage and quickly clipped the first part into place. As she maneuvered the rest of it into place she continued, "This should make it apparent that you have passed the audition, with flying colors, you certainly are everything I was hoping for."

If the cage hadn't already been restricting things, my imagination and knowing I'd 'passed' would have had me rising to the occasion, even after three really strong orgasms. Physically I could have easily stopped her from putting it on, but if it made her more comfortable, I was not going to kick up a fuss. Besides, I got a good look at the key as she clicked the small padlock onto the cage and it was everything I could do not to laugh. It was so simple that I could probably pick it with a paperclip. I had a full set of lock picks and the experience in using them in my workshop.

"What, you don't trust me? Why in the world would I want to do anything to mess this opportunity up?"

"Call it a mother's peace of mind. So, next Wednesday evening? I know you have classes Monday, Tuesday and Thursday."

I nodded, "I'm obviously not in a position to argue, Wednesday is free, I'll have more nights free once your community class finishes up in a few weeks. I'll have the chardonnay chilled."

She caressed my face with a smile, "Good, you are trainable! Lose the briefs and find some nice silky boxers, no pastels, something strong, black, red, blue would all look good on you. Leave the garage door unlocked and be lying here waiting. Open the wine and leave it on the counter, with two glasses before you come back. I'm leaving the restraints here."

"No introductions beforehand? And you know she is too young to drink!"

"I'm her mother and she can legally drink if she is with me and I allow it. You two already know each other, at least by sight. This isn't a blind date, it is an educational endeavor, though admittedly with some rather special benefits! Hmm, but perhaps I should put a mask on you? No, that would make it difficult for you to use that talented tongue of yours." I walked her to the door, the cage chaffing a bit as I had to learn to walk with it in place. She gave me a quick kiss on the cheek as she went out the door.

"See you next week!"

I waited until she was out of the driveway and locked everything up tight. Then I went to my office and dug out my lockpick set. It took a bit longer than I expected, but I was finally able to pop the lock without damaging it. It was more the fact the lock was so small and tucked away from my direct view that created the majority of the challenge. Having removed that element of restriction, I settled back into my normal routine to wait for Wednesday.

*****

Chapter 2 is in the works, so stay tuned!

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